


Preparation

by YlvaUllsdotter



Series: SPN Kink Bingo 2019 [19]
Category: Supernatural
Genre: Anal Fingering, Anal Plug, Angst, Asexual Character, Bottom Dean Winchester, F/M, Femdom, Fingering, Fluff, Smut, Sub Dean, Sub Dean Winchester, Sub!Dean, Submissive Dean Winchester, Supernatural Kink Bingo 2019, talking about boundaries
Language: English
Status: Completed
Published: 2019-10-19
Updated: 2019-10-19
Packaged: 2020-12-24 06:35:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,263
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21095018
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: Preparation is key to a pleasant experience.





	Preparation

**Author's Note:**

> Written for @spnkinkbingo. Square filled: Fingering
> 
> I apologize for nothing.

It had been almost a month since that night in the motel. Neither of them had said anything about it. In fact, they had more or less been avoiding each other the whole time. Whenever they were in the same room, Kat would catch Dean looking at her with forlorn eyes. She could not bring herself to talk about what had happened, mostly because she herself was confused about how she felt. 

On the one hand, he had clearly enjoyed himself, but on the other hand, she had more or less raped him. Something she had promised herself long ago that she would never do. Never go into a scene while angry or emotional. That was her rule, and she had broken it. Then there was the issue of Dean’s feelings for her. That had been clear enough in the way he spoke to her.

Today, finally, she felt ready to tackle the issue with Dean. The bunker was empty and would be for the rest of the day, at least. After she saw Sam off, she went looking for Dean. She found him in the garage, bent over the Impala’s engine, t-shirt and jeans covered in grease stains. She walked up next to the car, hands in her pockets. Dean glanced up at her briefly, immediately focusing back on the work at hand. She leaned her hip against the car, watching him, the way his hands handled the small parts of the engine. The silence between them weighed on her until she had to break it. She cleared her throat, making Dean glance up again. The look in his eyes made her heart clench. She had hurt him with her silence.

“So…,” she began, the single syllable echoing in the cavernous space.

Dean finished screwing something down with his fingers, then stood up and wiped the grease from his hands with a dirty rag. He said nothing, just looked at her with that hurt look in his eyes.

She took a deep breath and soldiered on.

“I’m sorry.” She looked back into his eyes, trying to convey her sincerity. “I hurt you, and I’m sorry, Dean.”

He stared at her, hands still, holding the rag. He cocked his head, then nodded curtly. Clearly, he was going to let her do most of the talking.

“Fair enough. I’m sorry for what I did, and I’m sorry for not talking to you all this time. I needed to get things straight in my own mind before talking to you about it,” she tried to explain.

Dean finally moved, tossing the dirty rag onto the toolbox on the other side of the car, and closing the hood. He leaned a hip against the front of the car and folded his arms across his chest. He cleared his throat as if his voice was rusty from disuse.

“That night, at the motel, you don’t have to apologize for that. The silence afterward was worse,” he finally got out.

Kat nodded, agreeing with him about the latter part at least.

“I know.” She reached her hand out, hesitantly, moving slowly to give him a chance to move away. He did not, and her hand ended up on his arm, his skin cool to her touch. “If you want to, I’m ready to talk now. I’ll be in my room if…” She trailed off and dropped her hand at her side.

With that, she turned and walked away, heading to her bedroom. She had barely made it to the doorway leading to the bunker hallway when she heard the tread of Dean’s boots behind her. 

His longer legs carried him to her side in two long strides and he walked beside her through the hallways in silence. They got there without passing any of the common areas and when she stepped ahead of him to enter her room, she caught him checking up and down the hallway for other people. The room was not that large; by the time she had sat down at the foot of the bed, he was only just taking a step inside and turning to close the door behind them. His movements were deliberate and when he turned back around she saw the same forlorn look in his eyes that she had gotten unfortunately used to in the past weeks. 

She gestured for him to sit in the padded armchair she had dragged in there for comfort, and he moved over and sat down on the edge of the seat, resting his forearms on his knees. She folded her hands on her lap and took a deep breath.

“I know you said I didn’t have to apologize for what I did that night but I am sorry. I broke my own rule. That’s partly what caused me to avoid you all this time. It...confused me,” she began, making herself look at Dean the whole time.

He tilted his head inquisitively and she bobbed her head in a small nod.

“Right. I’ve always had as a rule to never do any kind of kinky stuff while angry or emotional. It never ends well, as you’ve seen.” She sighed, one of her hands coming up to pinch the bridge of her nose. “The emotions confused me. I...guess I wasn’t prepared to feel so much so quickly.” She dropped her hand back down and searched Dean’s eyes for understanding.

The little crease between his eyes had appeared, signaling his confusion. At the same time, in his eyes, she thought she could see a glimmer of hope. He stayed silent though, waiting for her to continue.

“I guess what I’m trying to say is that I like you as a lot more than just a friend, Dean. That’s why I got upset in the first place, even though I didn’t realize it at the time.” She paused and took another deep breath. 

Dean flashed a tiny smile, just a curving of his lips, there and gone almost before it registered. He started to speak but stopped himself when she held a hand up.

“Please, Dean, let me finish. Ok?”

He nodded and scooted back on the seat, finally letting himself relax, at least marginally. She cocked her head, her expression going soft.

“I’ve known for a while how you feel about me, Dean. Sam let it slip one morning. He thought you had already told me, so don’t be mad at him. It was another thing that confused me.” She paused and sighed. “You know my story. I think I closed that part of me off to avoid getting hurt again, and I guess it made me blind to cues I otherwise would have picked up.” She shrugged awkwardly. “It took you making me jealous for me to finally open that door and let myself feel again. I’m just sorry it also took me hurting you,” she finished.

Dean startled her when he stood up. He dragged the armchair closer before sitting back down and taking her hands in his.

“Honey, please stop apologizing. Yes, the silence hurt, but I get it. You needed time to process. You’re right, I do have feelings for you. I love you. I have for a long time. I just never thought you could feel the same for me.” He stopped to take a deep breath. “When you made your offer, to explore with me, I let myself have hope. When it didn’t lead to anything other than the physical play sessions, it frustrated me. That’s one hundred percent on me.” He squeezed her hands gently. “Now that I know you feel the same, I can be patient.”

She chuckled, and he tugged on her hands playfully.

“You know what I mean,” he smiled wryly. “You take the time you need to process your feelings, and I’ll be here.” His eyes got a sparkle of mischief. “I’m yours, remember?”

She rolled her eyes affectionately at the reminder.

“Dork,” she scoffed, then became serious again. “But, Dean, you have to understand that, regardless of my feelings, I’m still not going to want to have sex with you,” she told him, her voice laced with apprehension.

Dean made a face and nodded.

“That’s fine. I can live with that. But you’re gonna have to give me some ground rules for what’s acceptable and what’s not.”

“I can absolutely do that,” she nodded, giving his hands a squeeze. “For now, I’d really like a hug though.”

Dean shifted to sit on the bed next to her, wrapping his arms around her without another word. She moved closer and rested her head on his shoulder, his heartbeat directly beneath her ear, and let him envelop her. She sighed contentedly when Dean rested his cheek on the top of her head. One large hand rubbed soothing circles between her shoulder blades, making her hum happily. The smell of engine grease was pervasive, but underneath it, she could smell Dean.

“I like this,” she mumbled, “this is nice.”

His rumble of agreement vibrated through her and she turned her head, her lips finding the soft skin at the juncture of his neck and shoulder. His sigh sounded like a storm in her ear. She did nothing else, simply let her lips press against his skin, enjoying the soft sensation.

After a while - she had no idea how long - she stirred and began to pull away. Dean immediately released her and sat back. She brushed two fingertips over the spot where her lips had been, and he shivered. Her lips quirked into a smile and she cocked her head looking at him.

“What,” he asked, his tone playfully worried.

“You’re mine,” she whispered softly, cradling his face in her palm, her thumb softly tracing his bottom lip.

He stayed silent until she moved her thumb away, then smiled wryly.

“I think we established that.”

“Smartass,” she affectionately shot back.

“Always,” he grinned.

“I want to do it right,” she told him. “If you’ll let me.”

It took him a moment to realize what she was talking about, but when he did he nodded.

“Take your clothes off,” she whispered.

Dean slowly pulled away from her touch and stood up. He did not try to show off, but simply removed the layers of fabric at a regular pace. The whole time his eyes were locked on hers. The clothes ended up in a messy pile on the seat of the armchair until he stood completely naked in front of her.

It was hardly the first time they had been in this position but this time was different. They both felt it. This time they were both aware of each other’s feelings and it made the moment somehow more intimate.

She reached out to slide her hands up the outside of his thighs, to his hips and up to his waist. Goosebumps erupted on his skin and she felt as if his feelings for her were written on his body in braille. 

Looking up at him, she rested her hands on his hips. 

“Fetch it for me,” she whispered. “Top drawer.”

He moved away from her touch reluctantly, going straight to the dresser and pulling out the top drawer. She stood up next to the bed, watching him. He drew a shaky breath before he reached in to grab what she wanted. Meanwhile, she peeled her jeans off, kicking them aside, then dropping her t-shirt on top of them. By the time Dean was in front of her again, she was in her bra and panties, waiting for him.

“Put it on,” she instructed him.

Dean dropped to his knees in front of her, arranging the straps before holding it out for her to step into. He slid it up her legs until he could fasten the strap around her waist to hold it in place while he adjusted the other straps. She felt his hands tremble whenever he touched her. When he was done, she cupped his chin and tilted his head up to look into his eyes. She smiled softly, making him relax and exhale, his shoulders falling when the tension bled out of them.

“Such a good boy,” she praised him, keeping her voice soft. “Don’t worry, Dean, I’ll take good care of you.”

She brushed her fingers through his hair, enjoying the sensation of the short hair tickling her palms. Leaning down, she kissed his forehead, then slid her hands to his shoulders. She nudged him along gently.

“On your back, pet,” she instructed, and he hurried to obey.

One hand on her hip, the other gripping the base of her silicone cock, she watched while Dean shifted around until he was flat on his back in the middle of the bed, arms at his sides. He watched her, breathing hard through his nose, his expression letting her know he was looking forward to what was coming.

Moving to the other side of the bed, she got the bottle of lube out of the nightstand drawer, setting it on top. 

“Hands above your head, Dean,” she told him and waited until he had complied before getting on the bed.

She moved his leg, getting him to bend it at the knee and placing his foot flat on the mattress. Before she had finished, he had already moved both legs into position. She nudged his knees gently until he had spread his legs to her satisfaction. Moving the bottle of lube to the bed, she shifted to kneel between his legs. 

Her hands caressed his legs from ankles to knees, then moving to his inner thighs where she lightly scraped her nails on the sensitive skin. She watched him hold his breath when her hands came near his cock, then exhale frustratedly when she skipped over it and continued her stroking from his groin to his nipples, then back. Again, she skirted the one place he really wanted her to touch and watched his cock twitch. Instead, she cupped his ass in her hands, her thumbs kneading the flesh on either side of his crack, massaging his taint. She pulled his cheeks apart and blew softly over the sensitive area, then rubbed her thumbs down either side of his puckered muscle and watched it clench in anticipation.

“Relax, pet,” she whispered, never stopping what her hands were doing.

“I’m trying,” he panted, his voice strained with tension.

“Try harder,” she teased him. She nodded towards his hands. “Gimme your hands,” she told him and waited for him to obey.

“Here,” she said, moving his hands until he was holding himself open for her.

She watched his face while she brushed a single fingertip lightly over his tight muscle. His lips parted and his head fell back against the pillow when a choked grunt punched its way out of his chest. 

“Told you I’d make you feel good,” she smirked.

With her free hand, she grabbed the bottle of lube and popped the top. Squeezing out a generous dollop onto her other hand, she went right back to massaging the slippery substance into Dean’s skin, drawing tight circles around his hole, working to relax the muscle.

By the time she slipped her index finger inside him, Dean’s ass was well and truly lubed. The finger slid in easily to the first knuckle where she stopped and moved it in and out slowly while watching Dean’s face. It was a sight to behold. Lips parted around short shallow breaths, eyes closed, head tilted back, skin flushed. She wished she could capture the way he looked at that moment, in the soft light of the room. Like a renaissance painting; Angel in Ecstasy. And she had only just begun.

She kept up the slow shallow thrusts until she heard Dean beg.

“Please. More. I need...more.”

Without saying a word she slid the finger deeper, all the way inside him, to the sound of his drawn-out moan. She held still there until Dean started trying to thrust his hips.

“Tell me what you need, pet,” she prompted him softly.

“More, please, Kat. Feels so good,” he begged breathily, the flush of his face spread now to his chest.

“Since you said ‘please’,” she teased.

She slid the finger almost all the way out, slowly, then just as slowly back in, rotating it until she could feel the soft patch of tissue inside him with her fingertip. She crooked the finger, rubbing his prostate and drawing a high-pitched whimper from Dean.

“Fuck! Please. Right there. Please, more,” he begged, almost desperately.

Giving the spot her attention for a moment, she pulled the finger back out, to Dean’s frustrated groan.

“Patience, Dean,” she admonished affectionately while adding more lube.

She worked the single finger inside him until she judged that he was sufficiently relaxed to take another. When she pushed the two fingers inside him, Dean tensed for a moment, then forced himself to relax. His face scrunched in discomfort and he breathed slowly while she inched both fingers inside him. The copious amounts of lube helped ease the way, but she knew he would be feeling some discomfort until she worked him open. Once both fingers were all the way in, she rewarded him by massaging his prostate. His cock, lying heavy against his stomach, was leaking pre-come, while he begged for something, anything, more.

Adding more lube, she set the bottle aside and rested her now free hand on Dean’s hip, rubbing soothing circles into his skin. Her two fingers inside him alternated between scissoring and massaging his prostate and he was breathing hard; little breathy whimpers escaping his parted lips. Lips that were dry now from panting.

“Please. I need...uhh...fuck!” Dean was almost babbling now.

She could have watched him like this for hours, strung out and wrecked, completely at her mercy. She had other plans though and so, before he got too close to the edge, she pulled the two fingers out and wiped her hand on the washcloth she kept in her nightstand.

Dean whimpered needily when she got off the bed, his eyes following her. She went to the dresser and pulled out the plug Dean had enjoyed so much the first time they tried it. With Dean stretched out, and the amount of lube in and around his ass, there was no need to add more. The plug slid in easily, settling into place as if it belonged there. Dean groaned at the familiar feeling. She moved his hands and pushed on the plug to make sure it was seated properly, then nudged him to lower his legs. The change in position made Dean moan again when he felt the plug move inside him, pressing against his prostate.

Grabbing her phone from the pocket of her discarded jeans, she pulled up the app for the plug and turned it on, setting it to a slow pulsing pattern with low vibration. Just enough to keep Dean on edge, but not enough to push him over.

She leaned in and kissed his cheek.

“Stay here, pet. I’ll be right back, ok?” She spoke softly and waited to make sure he had heard and understood her.

Dean nodded jerkily, his body tense on top of the bed, hands gripping the blanket. The continued stimulation to his prostate had him wound up like a tightly coiled spring, muscles trembling with tension.

She paused at the side of the bed and looked down at him. Stretched out on the bed, skin flushed, eyes glazed over with need, glistening with sweat, he was beautiful. And all hers.

**Author's Note:**

> Previously Reader Insert. See work Spring Break for more info.


End file.
